This paper is in line with research that analyzes the careers of European parliamentarians, adopting a comparative and cross-sectional approach and taking into account previous and subsequent political experiences in a multilevel perspective. Indeed, we propose a comparison between two similar cases, namely two southern European countries that have a quasi-federal system or are affected by an important regionalization process – Spain and Italy – and we examine a rather long time period ranging from the IV to the IX EP legislature. Our dataset consists of 508 observations, 195 relating to Spanish members of the European Parliament (MEPs) and 313 to Italian ones. By relying on the recent systematization, we propose to classify MEPs’ career models – which are our dependent variable – into four types: the EU shorter-termers, the ‘stepping stone’ MEPs, the EU long-termers, and the ‘multilevel surfers’. A multinominal regression analysis was conducted to understand which political factors (party affiliation of MEPs, length of previous career, critical European Parliament [EP] elections) may have a specific impact on each career type. We found that, after the 2014 EP critical election, the probability of MEPs engaging in the EP decreases, as they are more likely to develop a short-term career model than a long-term one. In addition, previous national experience and a regional executive career are the best predictors of a multilevel career.